Condensation product of the diethyl ester of methelene-disalicylic acid-di(p-amino benzyl ether) with pyruvic acid



Patented July 7, 1931 UNITED STA E- FA OFFICE I i mom LEWIS SUMMERS, or rear wean-matron. BENNSXL ANIA CQNDENSA-TJION PRODUCT o as DIE'THYL BS1133 r nrrastrnanisem mis acm- EB-AMINO BENZYL ETHEE) WITH syn-owe e011.

No Drawing. Application filed October 30, 1924. Serial No. 746,868.

' This invention relates to synthetic organic hundred gallons of clean water to which sufehemical compounds used in pharmacy and ficient caustic soda is added to give analkait has for an object to provide an effective line reaction, when three hundred and fifty remedy for the treatment of uric acid dispounds (350 lbs.) of sodium hydrosulphite is orders and the various ailments developed gradually added with the temperature of the by the-presence of such acid in the human mass maintained SOTC. for eight hours. system. The organic compound resulting ispreci'pi- With the, foregoing object in VieW'my-intated out of the solution by means ofmuriatic vent-ion consists of a novel process and new acid in sufficient amount to turn congo test composition of matter characterized by high paper blue. The reaction-and its product therapeutic properties, and hence is destined a b s nt d as follo as a pharmaceutical preparation for the ef- 000E fective treatment of uric acid diathesi s, rheumatism, anthritis, gallstone, glycosuria O;N

and kindred disorders. r

-oomuoz concrete example, I unite two salicylic acid molecules in a condensing reaction. By the reaction thereon of formaldehyde, one hydrogen atom in each of the salicylic acid groups is removed while the formaldehyde is deprived of its oxygen thus leaving the methylene group CH The reaction and its product may be represented as follows:

In carrying out the invention, and as a boon CDQH lznansowmo /OOOH c0011 C The product of the reaction is mixed with one O hundred and forty pounds (1&0 lbs.) of ethyl C 0 alcohol at a temperature below- C3,, and 2 COOH one hundred pounds lbs.) of sixty-six degree sulphuric acid is gradually added so that the temperature does not advance beyond theafore said degree (70 After this compound are converted into its sodium l h suiphumcimd 1S addedithe tempera" salt and heated'to 150 C. with three hundred f 1s slowly reused during. f hours to and forty-three pounds of paranitrobenzyl 0' i l n lts P d may chloride-or either of the tWo isomers of this represented as follows:

Two hundred and eighty-eight pounds of nitrobenzyl compound. The reaction and its OH I product may be represented as follows: p

G O OH pg -0 CH;-C NH;

raj +2CzH5OHr I +2CIOH2ONOZ l H20 COOH COOH' 0000111; OH V; 00011 7 O H2 +1101 l i \OOGH O- v i 4 00 02 m The resultant reaction product is washed v 00011 in clean Waterand heated to 120 C. for two The product of this reaction is heated in three hours with one hundred and seventy-six pounds (176 lbs.) of pyruvic acid, after which the condensation product of the diethyl ester of methylenerdisalicylic acid-di (p-amino benzyl ether) with pyruvic acid, or methylene m m diethylsalicylate-p p di (ppyruvyl-amino-benzyl ether) is thoroughly pulverized. This product C H N O is an amorphous powder, brown in color, insoluble is water, slightly soluble in chloroform and freely soluble in ethyl alcohol. 'The reaction and its product may be represented as follows:

+2HO CO C O UHF Q0 omONm C O O (EH5 Hz-ONHCOCOOH: Hz-O-NHCOCOOH;

COOCzHs In this case the empirical composition is, of course, different from that given above.

This new pharmaceutical composition of matter when administered as an internal medicine in doses of ten to fourteen grains, ac-

signed my name at Philadelphia, Pennsylvania, this 3rd day of October, 1924.

SAMUEL LEWIS SUMMERS.

cording to the condition of the patient, will be found a valuable remedy and curative in cases of uric acid diathesis, rheumatism and anthritis; as well as extremely beneficial for the elimination of gallstones and glycosuria.

Although I have given certain quantities and proportions for the various ingredients in the preparation of my new composition of matter, it is to be distinctly understood that the same are by way of a concrete example only, as they may be varied to react a predetermined quantity without departing from the scope of this invention. Likewise the time periods hereinbefore stated as involved in the several stages of the process are not to be considered arbitrary, they likewise, being susceptible of change without materially affecting the resultant reaction. Accordingly the right is hereby reserved to make such changes as reasonably lie within the ambit of the appended claims.

Having thus described my invention I claim i 1. The hereindescribed condensation prod not of the diethyl ester of methelene-disalicylic acid-di (p-amino benzyl ether) with pyruvic acid, insoluble in water, but slightly soluble in chloroform and freely soluble in ethyl alcohol. .7 r

2. The process of producing the hereindescribed organic product which comprises condensing two molecules of salicylic acid with formaldehyde, forming the sodium salt of 

